ANNA MARIA ISLAND – Alleging a “deliberate, bad faith scheme” related to a $105 million deal struck with Prime Business in 2024, StayTerra Vacations has filed a civil lawsuit against Kiri Stewart, Magnolia Cottages LLC and 10 additional LLCs.
Filed on Dec. 19 with the 12th Judicial Circuit Court in Bradenton, the lawsuit names as plaintiffs StayTerra Vacations LLC, Prime Vacations LLC and GSP Prime Holdings LLC.
The lawsuit names as defendants Kiri Stewart, Magnolia Cottages LLC, 48 Street LLC, 9801 Gulf Drive LLC, 224 Chilson Ave. LLC, 243 S. Harbor Dr. LLC, 518 Spring LLC, 2403 Avenue C LLC, 128 Fillmore LLC, 2210 Avenue A LLC, 103 Park Ave. AMI LLC and 6548 Sabal Dr. LLC.
Developer Shawn Kaleta is not named as a defendant, but he’s mentioned in the lawsuit and he’s listed with the Florida Division of Corporations as the manager of five of the 10 property-specific LLCs named as defendants in the lawsuit.
The lawsuit complaint says the plaintiffs, StayTerra, seek “equitable relief to enforce their agreements with the defendant Seller-KS Property Companies (Stewart’s LLCs) and to recover damages to compensate them for the substantial losses they have already incurred as a result of the defendants’ intentional and material breaches of their contractual obligations.”
“By reason of the deceptive and unfair trade practices employed by defendants Stewart and Magnolia Cottages, plaintiffs have suffered damages in excess of $5 million,” the complaint alleges.
“The founders and owners of the Prime Business who bound the defendant, Seller-KS Property Companies, to the Master PMA (Property Management Agreement) were Shawn T. Kaleta and Roman Eckert, the ‘Founders and Owners’. One of the founders and owners of Prime Business is defendant Stewart’s romantic partner and the father of her children,” the complaint says.
“Plaintiffs respectfully requests this court enter judgement in favor of plaintiffs against defendants, award plaintiffs compensable damages in an amount to be proved at trial, but an amount not less than $5 million, in addition to a temporary restraining order, preliminary injunction and permanent injunction prohibiting the defendants from continuing to engage in unfair and deceptive trade practices,” the complaint says.
The case is assigned to Circuit Court Judge Charles Sniffen.
StayTerra is represented by the Sarasota-based Williams Parker Harrison Dietz & Getzen law firm and the New York City-based Paduano & Weintraub law firm.
The lawsuit
According to the lawsuit complaint, GSP is an investment firm founded in or around 2013 with assets under management of more than $3.5 billion.
“Garnett Stations Partners (GSP), through plaintiff, StayTerra and GSP Prime Holdings, paid approximately $105 million to acquire the outstanding equity interests in Prime and other companies comprising a vacation rental management business,” the complaint says.
“In or around late 2023, GSP identified a potential opportunity in the large, growing and highly fragmented vacation rental management industry. Eventually, in or around January 2024, GSP received an introduction to a prominent real estate developer in Southwest Florida who had founded and built a vacation rental management business comprised of six brands (AMI Locals, Anna Maria Island Accommodations, Anna Maria Vacations, Siesta Key Luxury Property Rentals, Lido Key Vacations and Tropical Sands Vacations), referred to herein as the ‘Prime Business,’” the complaint says.
At the time, Prime Business managed approximately 1,110 vacation rental properties, including approximately 130 properties that were indirectly owned or controlled by the founders of Prime Business through the defendant, Seller-KS Property Companies and certain other LLCs, according to the complaint.
“The founder and owners of the Prime Business recognized that they needed liquidity for their real estate development business and also that GSP was an ideal partner to assist with scaling the Prime Business into a national player in the vacation rental management industry,” the complaint says.
On or around Sept. 18, 2024, GSP, through StayTerra, closed on a transaction with the founders, owners and certain other seller entities to acquire a majority stake in Prime Business.
“The deal was structured through an Equity Purchase Agreement (EPA) pursuant to which plaintiff StayTerra acquired all of the equity interests in Prime and certain other companies comprising Prime Business for a purchase price of approximately $105 million – consisting of approximately $70 million cash and approximately $35 million in rollover equity in GSP Prime Holdings, the ultimate parent company that owns StayTerra,” the complaint says.
Pursuant to conditions of the EPA, the owners/founders of Prime Business agreed they would not do the following for a period of five years:
- Compete with Prime Business (StayTerra)
- Recruit or hire any employee, service provider or independent contractor of the Prime Business to leave the employ or cease providing service
- Contract with any suppliers of Prime Business
The complaint notes each of the founder/owners of Prime Business entered into a contribution agreement with GSP Prime Holdings in which they agreed to contribute their personal goodwill that included close business relationships with customers and vendors, trade secrets and knowledge.
“As a condition to the closing of the transaction, the founders and owners of the Prime Business delivered a Master Property and Rental and Management Agreement,” the complaint says regarding 10 properties on Anna Maria Island or in Sarasota or Bradenton.
The LLCs for those 10 properties are listed as defendants. The Florida Division of Corporations lists Stewart as the manager of 224 Chilson Ave. LLC, 48 Street LLC, 9801 Gulf Dr. LLC, 243 South Harbor Dr. LLC and 128 Fillmore LLC. Kaleta is listed as the manager of 518 Spring LLC, 103 Park Ave. AMI LLC, 2403 Avenue C. LLC, 2210 Avenue A LLC and 6548 Sabal Dr. LLC. The Najmy Thompson law firm is named as the registered agent for all 10 of the property-specific LLCs named as defendants.
The Florida Division of Corporations lists Stewart as the manager and registered agent of Magnolia Cottages LLC.
According to the complaint, the founders and owners of Prime Business granted Prime the exclusive right to collect management fees for the properties for a minimum of seven years.
“Yet less than thirteen months after pocketing the consideration comprised of approximately $105 million of cash and rollover equity, the defendants embarked on a deliberate, bad faith scheme to eviscerate the benefit of the bargain plaintiffs struck by facilitating purported transfers of the founders’ membership interest in the Seller-KS Property Companies that are subject to the Master PMA to defendant Magnolia Cottages, which is ostensibly owned and controlled by defendant Stewart,” the complaint alleges.
The complaint alleges that in each of the transfer agreements, the founders and owners of the Prime Business, “falsely represented they had the full power to transfer their interests in the Seller-KS Property Companies subject to the Master PMA without obtaining the consent or approval of any other person.”
On Oct. 7, 2025, Stewart and Magnolia Cottages received a cease-and-desist letter from the plaintiffs.
“They were undeterred by that letter and have continued to actively engage in their scheme,” according to the lawsuit.
The complaint alleges, “Defendants Stewart and Magnolia Cottages have assisted the founders and owners of the Prime Business with a ‘shadow listing’ scheme for other properties that indisputably remain subject to the Master PMA.
“Specifically, defendants Stewart and Magnolia Cottages have listed properties that are owned or controlled by the founders of the Prime Business and subject to the Master PMA on Airbnb, VRBO and other booking platforms at prices that are lower than the prices offered by plaintiff Prime,’ the lawsuit further alleges.
Stewart response
On Monday, Jan. 26, Stewart provided The Sun with a written statement that said, “We will vigorously and successfully defend against these claims. The allegations made by Prime are false, misleading and without merit. Prime is a large corporate entity attempting to bully us as homeowners and small property operators by unlawfully seeking control of properties that we own outright.
“Prime previously mismanaged these properties, and we exercised our lawful right as owners to resume control. At no time did we sign away ownership rights or grant Prime authority to possess or control our homes,” Stewart stated.
“Had Prime successfully managed the properties and generated acceptable revenue, we would not have removed them from management. Since self-managing, we have significantly outperformed Prime’s results.
“This lawsuit is a transparent and failed attempt by a Wall Street–backed private equity firm to use the court system to pressure and exploit a small, local business rather than accept responsibility for its own mismanagement,” Stewart stated.
